spiraeoside
2-[4-(beta-D-glucopyranosyloxy)-3-hydroxyphenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one
Identification
| Name | spiraeoside |
| IUPAC | 3,5,7-trihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one |
| CAS Number | 20229-56-5 |
| EINECS | 243-614-6 |
| FDA UNII | K2B74751XI |
| Molecular Formula | C21 H20 C12 |
| Molecular Weight | 416.52240000 |
| MDL Number | MFCD00221723 |
| Nikkaji Number | J94.563C |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 835.60 °C. @ 760.00 mm Hg (est) |
| Flash Point | 562.00 °F. TCC ( 294.70 °C. ) (est) |
| logP (o/w) | -0.380 (est) |
| Soluble in | water, 2.159e+004 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | skin conditioning |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic ingredient for skin conditioning |
| Recommendation for spiraeoside usage levels up to | not for fragrance use. |
| Recommendation for spiraeoside flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 2-(4-(beta-D-glucopyranosyloxy)-3-hydroxyphenyl)-3,5,7-trihydroxy-
2-(4-(beta-D-
glucopyranosyloxy)-3-hydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
2-[4-(beta-D-
glucopyranosyloxy)-3-hydroxyphenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one
quercetin 4'-O-glucoside
spiraein
spiraeosid
3,5,7-
trihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
PubMed:
A nicotinic receptor-mediated anti-inflammatory effect of the flavonoid rhamnetin in BV2 microglia.
PubMed:
Relationship analysis between flavonoids structure and subcritical water extraction (SWE).
PubMed:
Polyphenol contents and antioxidant activities of extracts from flowers of two Crataegus azarolus L. varieties.
PubMed:
Spiraeosides A and B, two new diterpenoid glucosides from Spiraea japonica var. ovalifolia.
PubMed:
The crystal structure of human cytosolic beta-glucosidase unravels the substrate aglycone specificity of a family 1 glycoside hydrolase.
PubMed:
Antioxidant activity of Filipendula hexapetala flowers.
PubMed:
Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones.
PubMed:
Modulation of drug transport by selected flavonoids: Involvement of P-gp and OCT?
PubMed:
Disposition and metabolism of [2-14C]quercetin-4'-glucoside in rats.
PubMed:
In vitro digestion and lactase treatment influence uptake of quercetin and quercetin glucoside by the Caco-2 cell monolayer.
PubMed:
Ingestion of quercetin inhibits platelet aggregation and essential components of the collagen-stimulated platelet activation pathway in humans.
PubMed:
Quercetin glucosides inhibit glucose uptake into brush-border-membrane vesicles of porcine jejunum.
PubMed:
The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides.
PubMed:
Quercetin-4'-glucoside is more potent than quercetin-3-glucoside in protection of rat intestinal mucosa homogenates against iron ion-induced lipid peroxidation.
PubMed:
Absorption of quercetin-3-glucoside and quercetin-4'-glucoside in the rat small intestine: the role of lactase phlorizin hydrolase and the sodium-dependent glucose transporter.
PubMed:
Determination of flavonol metabolites in plasma and tissues of rats by HPLC-radiocounting and tandem mass spectrometry following oral ingestion of [2-(14)C]quercetin-4'-glucoside.
PubMed:
Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide.
PubMed:
Quercetin glucuronides but not glucosides are present in human plasma after consumption of quercetin-3-glucoside or quercetin-4'-glucoside.
PubMed:
Efficiency of absorption and metabolic conversion of quercetin and its glucosides in human intestinal cell line Caco-2.
PubMed:
Pharmacokinetics and bioavailability of quercetin glycosides in humans.
PubMed:
Interaction of quercetin glucosides with the intestinal sodium/glucose co-transporter (SGLT-1).
PubMed:
Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway.
PubMed:
Quercetin glucosides are completely hydrolyzed in ileostomy patients before absorption.
PubMed:
Cellular uptake of dietary flavonoid quercetin 4'-beta-glucoside by sodium-dependent glucose transporter SGLT1.
PubMed:
Efflux of dietary flavonoid quercetin 4'-beta-glucoside across human intestinal Caco-2 cell monolayers by apical multidrug resistance-associated protein-2.
PubMed:
Bioavailabilities of quercetin-3-glucoside and quercetin-4'-glucoside do not differ in humans.
PubMed:
Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase.
PubMed:
The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man.
PubMed:
Absorption and excretion of conjugated flavonols, including quercetin-4'-O-beta-glucoside and isorhamnetin-4'-O-beta-glucoside by human volunteers after the consumption of onions.
PubMed:
Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver beta-glucosidase activity.
PubMed:
Dietary quercetin glycosides: antioxidant activity and induction of the anticarcinogenic phase II marker enzyme quinone reductase in Hepalclc7 cells.
PubMed:
Absorption and disposition kinetics of the dietary antioxidant quercetin in man.
PubMed:
Densitometric evaluation of spiraeoside after derivatization in flowers of Filipendula ulmaria (L.) Maxim.
PubMed:
Induction of sister-chromatid exchanges (SCE), polyploidy, and micronuclei by plant flavonoids in human lymphocyte cultures. A comparative study of 19 flavonoids.
PubMed:
On the Occurrence of Kaempferol-4'-O-beta-D-glucopyranoside in Filipendula ulmaria and Allium cepa.
PubMed:
[Flavonols and flavones of vegetables. VI. On the changes of the flavonols of onions (authors transl)].
PubMed:
[Flavonols and flavones of vegetables. VII. Flavonols of leek, chive and garlic (author's transl)].